Aminohydroxy compounds as wetting agents



Patented Nov. 28, 1939 UNITED STATES -lameu'r OFFICE ENTS Jerome Martin, Terre Hante, Ind., assignonto Commercial Solvents Corporation, Terre Haute, Ind., a corporation of Maryland No Drawing.

Application August 25 1937, Serial No. 160,779

Claims. (Cl. 260-404) My invention relates to the use of the salts of aminohydroxy compounds as wetting agents, and the like. More particularly, it relates to the use of the higher fatty acid'salts of monoand poly- 5 hydroxyamino compounds as wetting agents.

Wetting agents have a wide application in industry and are used extensively in the dyeing and mercerizing of textiles and in the preparation of such substances as inks, insecticides, detergents, etc. The function of wetting agents is to assist the rapid and uniform penetration of solutions into materials such as fibres and fabrics, and the rapid, uniform wetting of otherwise difiicultly wettable materials. The presence of a relatively small amount (about 0.1%) of a good wetting agent in a solution is generally sufficient to obtain the desired result. Various types of substances that have been suggested in the past as .wetting agents are such compounds as: sulfonated oils, sulfonated high molecular weight alcohols, metallic soaps, substituted imido alkylols, etc. a character as not to act unfavorably upon the solutions used for treatment or upon the material being treated by the solution. They should also perform their function as wetting agents without the necessity of subjecting the material treated to a preliminary treatment such as cleaning.

I have now discovered that the higher fatty acid salts of certain of the hydroxyamines are particularly suited for use as wetting agents. The aminohydroxy compounds which react with the fatty acids to form the wetting agents of my invention have the following general formulae:

on NH: OH NH: OH

III )L'. R: H

wherein X represents hydrogen, an alkylol or an alkyl group containing from one to three carbon' atoms and Y hydrogen or an alkyl group in which the number of carbon atoms in X plus. Y is less than six; R1, R2 and R3 represent hydrogen or alkyl groups in which the number of carbon atoms in R1 plus R2 is less than four and the number of carbon atoms in R3 is less than four. Specific examples of compounds included in the first formula given above are the aminopolyhydroxy compounds: 2-amino-l,3-propanediol, 2-amino-2-methylol-1,3-propanediol, and 2-amino-2-isopropyl-1,3-propanediol. Compounds ineluded by the second formula are 2-amino-1- propanol, 3-amino-3-methyl-2-butanol, 4-amino- 5-methyl-3-hexanol, and 5-amino-4-octanol.

Wetting agents should be of such The above aminohydroxy compounds are readily prepared according to copending applications Serial No. 146,855, filed June 7, 1937, by B. M. Vanderbilt, and Serial No. 151,841, filed July 3, 1937, by K. Johnson. The process consists essentially of condensing aldehydes and nitroparaffins under suitable conditions to obtain nitrohydroxy compounds. These nitro compounds may be readily hydrogenated to give the aminohydroxy compounds indicated in the above structural formulae.

These new wetting agents and solutions containing them may be prepared in any desired manner. The aminohydroxy salt may be prepared directly by adding the amino compound to an equivalent amount of a higher fatty acid at room or elevated'temperatures and in the presence or absence of a solvent such as ethyl ether. The salts thus prepared may be added directly to the wetting solution. If desired, however, the fatty acid and the aminohydroxy compound may be added to the wetting solution in any satisfactory manner together or separately. The concentration of wetting agent to be usedwill vary widely depending upon the solution, the material to be wetted and the degree of wetting desired. I have found that one percent by weight is a suitable concentration of the wetting agent in a solution used for wetting heavy cotton cloth. Suitable concentrations of the wetting agent to be used, however, may be readily determined by simple experimentation. In cer .tain instances it may be desirable to use an excess of the fatty acid or of the aminohydroxy compound in the wetting agent in order to confer difierent properties upon the wetting solution. The choice of. the particular wetting agent of my invention to be employed will also depend upon the use to which it is to be put. A large variety of salts are available which may be prepared from any of the'higher fatty acids and the aminohydroxy compounds containing from two to eight carbon atoms.

It is to be understood that any of the higher fatty acids or mixtures thereof may be used for preparing the emulsifying agents of my invention'. For example, any of the fatty acids or mixtures thereof obtained by the saponification of an animal or vegetable oil may be used whether I they be saturated or unsaturated, substituted or .not substituted. Examples of fatty acids that clupanodonic, and ricinoleic acids. In general,

I have found that fatty acids "containing less than twelve carbon atoms are not as satisfactory for preparing the wetting agents of my invention as those containing from twelve to twenty or more carbon atoms.

The wetting agents of my invention may be used for preparing solutions to be used for a large number of different purposes, some of which have been previously indicated. Other uses of the wetting agents of my invention will readily occur to those skilled in the art.

What I claim is:

1. A wetting agent consisting essentially of a higher fatty acid salt of an aminohydroxycompound of the following structural formula:

i 0H NH, on,

H (lJ-CY wherein X represents a constituent chosen from the class consisting of hydrogen and alkylol and alkyl groups containing less than four carbon atoms, and Y represents a constituent chosen from the class consisting of hydrogen and alkyl groups in which the number of carbon atoms in X plus Y is less than six.

2. A wetting agent consisting essentially of a atamsa higher fatty acid salt oi? 2-amino-2-n-propyl-' 1,3-propanediol.

.3. A wetting agent consisting essentially of the oleic acid salt of 2-amino-2-n-proply-L3- propanediol.

4. A wetting agent consisting essentially of the oleic acid salt of 2-amino-2-methyl-L3- propanediol. V

5. A'pr'ocess for improving the wetting power of an aqueous solution for solid surfaces, which comprises incorporating in said solution a higher fatty acid salt of an aminohydroxy compound of the following structural formula:

wherein X represents a constituent chosen from the class consisting of hydrogen and alkylol and alkyl groups containing less than four carbon atoms, and Y represents a constituent chosen from the class consisting of hydrogen and alkyl groups, and in which the number of carbon atoms in X plus Y is less than six.

JEROME MARTIN. 

